Synthesis of novel fluorescence probes and their application in the enantioselective recognition of arginine

Abstract

Arginine (Arg) plays a crucial and multifaceted role in various biological processes, encompassing cell division, wound healing, immune system modulation, and plant signaling. This study introduced a pair of novel chiral fluorescent probes, (R)-5 and (S)-5, constructed upon the BINOL framework, which exhibited enantiomeric selectivity and sensitivity to D-Arg/L-Arg in fluorescence experiments. These probes offered a simple, rapid, low-cost, and highly selective method for detecting Arg enantiomers, thereby providing a highly sensitive approach for their qualitative and quantitative analysis. The enantioselective fluorescence enhancement ratios {ef = [(I₁ − I₀)/(I₂ − I₀) = ΔI₁/ΔI₂]} of (R)-5 and (S)-5 to Arg were 1694 and 5163, respectively. Moreover, the probes demonstrated the capability to detect the concentration of D-Arg and L-Arg with a limit of detection of 4.84 × 10⁻⁷ M and 3.35 × 10⁻⁷ M, respectively, as well as determine the enantiomeric excess. These probes exhibited high chemical selectivity and enantioselectivity, enabling the identification of different configurations of Arg, quantification of Arg concentrations, and determination of the enantiomeric composition of Arg. This study provides valuable insights for the development of sensitive and selective chiral molecular detection methods, significantly advancing our comprehension of the relationship between Arg concentration and probe fluorescence response.